365 day to fall in love with Mr. Mafia Boss

365 day to fall in love with Mr. Mafia Boss

last updateLast Updated : 2026-07-01
By:  Geldiejay VallejosOngoing
Language: English
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Isabella Rossi has 48 hours to come up with €300,000 or her brother Luca disappears permanently. Luca gambled with the wrong man — Alessandro De Santis, Il Capo of Milan’s most feared crime family. When Isabella storms into his club to beg for mercy, Alessandro offers her a deal instead of a bullet. One year. Live at his Lake Como estate. Be his on paper when he demands it. Follow his rules. After 365 days, the debt is erased and her brother walks free. Break the contract early, and Luca pays with blood. To Alessandro, Isabella is just a new experiment. Politicians, cops, rival bosses — they all break within days of meeting him. He’s curious how long it takes a woman with nothing left to lose. To Isabella, Alessandro is a monster in a tailored suit. Cold, controlling, and lethal. Rule #1: Don’t fall in love with me. Easy, she thinks. She hates him. But the estate isn’t a prison of iron bars. It’s gilded cages, midnight conversations in the library, scars he doesn’t explain, and a man who watches her like she’s the only threat he can’t neutralize. The more rules he makes, the more he breaks them himself. Protection turns into possession. Glances turn into touches. And the contract’s fine print becomes a countdown neither of them can escape. Because Alessandro has enemies who want his empire, and now they want her too. When Luca’s betrayal runs deeper than debt and Isabella becomes a target, Alessandro has to choose: the empire he killed to build, or the woman he swore was just collateral. 365 days to survive him. 365 days for him to ruin her. 365 days to fall in love with the last man she should ever trust.

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Chapter 1

Episode 1: The Contract

365 Days to Fall in Love with Mr. Mafia Boss

The rain in Milan smelled like gasoline and wet stone. I pulled my coat tighter, but the February chill had already settled into my bones. Not that I could afford to care about comfort. Not when I was standing outside Velluto Nero, the club everyone in the city whispered about but no one admitted to entering.

They said the owner didn’t have a name. Just a title: Il Capo. The Boss.

I wasn’t here for rumors. I was here because my brother owed him €300,000. And as of three days ago, Luca had vanished.

The bouncer didn’t ask for ID. He just looked at the photo on his phone, then at me, and stepped aside. My stomach dropped. They’d been expecting me.

Inside, the club was nothing like I imagined. No pounding music. No bodies grinding in the dark. It was silent, opulent, and cold. Black marble floors, gold-veined columns, and a single chandelier that threw fractured light across the room like broken glass.

And at the center of it all, behind a desk of ebony wood, sat him.

Alessandro De Santis.

I knew his face from the papers—when they dared to print it. Sharp jaw, black hair combed back, suit tailored like it was armor. But the photos didn’t capture his eyes. Gray like a storm over the Tyrrhenian Sea, and just as unforgiving. He didn’t look up when I approached. He just turned a page in the ledger before him.

“Isabella Rossi,” he said, voice low, amused. “Twenty-four. Graphic designer. No criminal record. One brother, Luca, who seems to have misplaced a considerable amount of my money.”

My throat was dry. “I’m here to make a deal.”

That got his attention. He closed the ledger with a soft thud and finally met my gaze. Up close, the scar across his left eyebrow was faint but precise. A calculated mark. Nothing about him was accidental.

“You don’t have anything I want,” he said flatly.

“I’ll work it off. However long it takes. I’m not leaving until we have terms.”

He stood. He was taller than I expected, and the way he moved—slow, deliberate—made the room feel smaller. He circled the desk until he was in front of me. Too close. I could smell his cologne: cedar, smoke, something darker.

“People don’t negotiate with me, Miss Rossi. They pay. Or they disappear.” He tilted his head. “Your brother chose the second option.”

Panic clawed up my ribs. “He’s not dead.”

“No.” Alessandro’s lips curved, but it wasn’t a smile. “Death is merciful. And I’m not in a merciful mood.”

He walked back to his desk and pulled open a drawer. He slid a folder across the polished surface.

“Your brother borrowed money to cover his gambling debts. He promised collateral he didn’t have. He lied to me.” He tapped the folder. “I don’t forgive lies.”

I opened it. Photos of Luca, timestamps, bank transfers. And at the bottom, a contract. My eyes skimmed it, and my blood went cold.

365 days. Exclusive services to be rendered to Alessandro De Santis. Debt cleared upon completion. Early termination results in forfeiture of collateral.

Collateral. Luca.

“You want me to—” I couldn’t say it.

“I want what’s mine,” he interrupted. “Your brother traded your name before he ran. Said you were ‘valuable.’ I disagreed. Until now.”

He was studying me like I was a painting he couldn’t decide whether to buy or burn.

“You’ll live in the estate on Lake Como. You’ll follow my rules. You’ll be seen with me when I require it. In return, your brother breathes for another year. After 365 days, the debt is gone. You walk free.”

“And if I refuse?”

He didn’t blink. “Then I find Luca. And I make you watch what happens to men who steal from me.”

The room tilted. This wasn’t a choice. It was a blade pressed to my throat.

“Why a year?” My voice shook. “Why not just—”

“Because I’m curious,” he said, cutting me off again. He stepped closer, and this time his fingers brushed my chin, forcing me to look up. His touch was cold. “Everyone breaks, Isabella. The politicians, the cops, the other families. They all beg or bargain within a week. I want to see how long it takes you.”

It wasn’t desire in his eyes. It was calculation. I was a new game. A puzzle.

“One year,” I whispered. “No… extra conditions?”

His thumb dragged along my jaw, slow. “I don’t need to force women into my bed. They come willingly. The contract is for your time. Your presence. Your loyalty. What happens beyond that…” He let go, and I stumbled back half a step. “Is up to you.”

Liar. The way he looked at me said he already knew how this would end.

I thought of Luca—reckless, stupid, but still my brother. The only family I had left since our parents died. I thought of the men Alessandro had ruined. The stories about concrete boots and lakes that didn’t give up their secrets.

I picked up the pen on his desk. It was heavier than it should have been.

“If I do this, he’s safe? You won’t touch him?”

“You have my word.”

The word of a mafia boss. Worth nothing. Worth everything.

I signed. Isabella Rossi. The ink bled into the thick paper.

Alessandro took the contract, examined my signature, and slid it back into the folder like it was a receipt for coffee.

“Driver will take you to the estate tonight. Pack one bag. You won’t need much.” He sat back down, dismissing me already. “Oh, and Isabella?”

I paused at the door.

“Rule one,” he said, without looking up. “Don’t fall in love with me.”

I almost laughed. “Don’t worry. I hate you already.”

That made him look up. And for the first time, his smile was real. Sharp. Dangerous.

“We’ll see,” he murmured. “Day one starts now.”

Outside, the rain had stopped. But I was still cold.

365 days.

To pay a debt I didn’t owe.

To a man who collected souls like interest.

To survive.

I didn’t know it yet, but the clock had already started ticking. And Alessandro De Santis never lost a bet.

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